Shelter Island Vacations
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Where to stay in Shelter Island
Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
The room Was ready early and spotless The stuffy lobsters for the girls was a nice touch
Reviewed on Feb 16, 2026
Sound View Greenport
Hotel complaints Extra unknown/ non-disclosed charges- 13 arrival and 15 checkout **there are more charges than shown in Expedia Rooms not matching pictures (told to have an ocean view when not the case) Some ice on road/ sidewalk (seen someone slip) Disappointing “continental” breakfast Parking ...
Reviewed on Feb 15, 2026
Montauk Manor
Room was very nice
Reviewed on Feb 17, 2026
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
